EP0406700A1 - 3-Anilino-benzisothiazoles et fongicides les contenant - Google Patents

3-Anilino-benzisothiazoles et fongicides les contenant Download PDF

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Publication number
EP0406700A1
EP0406700A1 EP90112326A EP90112326A EP0406700A1 EP 0406700 A1 EP0406700 A1 EP 0406700A1 EP 90112326 A EP90112326 A EP 90112326A EP 90112326 A EP90112326 A EP 90112326A EP 0406700 A1 EP0406700 A1 EP 0406700A1
Authority
EP
European Patent Office
Prior art keywords
hydrogen
alkyl
haloalkyl
formula
halogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP90112326A
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German (de)
English (en)
Other versions
EP0406700B1 (fr
Inventor
Juergen Dr. Schubert
Jochen Dr. Wild
Helmut Dr. Hagen
Gerhard Dr. Nilz
Hubert Dr. Sauter
Eberhard Dr. Ammerman
Gisela Dr. Lorenz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
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BASF SE
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Priority to AT90112326T priority Critical patent/ATE104288T1/de
Publication of EP0406700A1 publication Critical patent/EP0406700A1/fr
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Publication of EP0406700B1 publication Critical patent/EP0406700B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the present invention relates to new, valuable 3-anilino-benzisothiazoles, processes for their preparation, fungicidal compositions containing these compounds and their use as fungicides.
  • 2-anilino-benzothiazoles for example 2- (2,6-dinitro-3-chloro-4-trifluoromethylanilino) -6-methoxybenzthiazole or 2- (2,6-dinitro-3- chlor-4-trifluoromethylanilino) -6-nitrobenzthiazole (EP 244 705), show a good fungicidal activity. However, the effect is not always satisfactory at low application rates and application concentrations.
  • alkyl itself or as part of another substituent, such as haloalkyl, alkoxy, alkylthio, haloalkoxy, is to be understood as meaning the following straight-chain or branched groups, depending on the number of carbon atoms indicated: in particular C 1 -C 4 -alkyl, methyl, ethyl, n -Propyl, iso-propyl, n-butyl, sec.-butyl, iso-butyl, tert.-butyl, n-pentyl, n-hexyl.
  • the prefix halogen in the designation of a substituent means here and below that this substituent can occur one to more times.
  • Halogen represents F, Cl, Br or J.
  • Haloalkyl thus represents a mono- to perhalogenated alkyl radical, such as CH 2 CI, CHCI 2 , CCl 3 , CH 2 F, CHF 2 , CF 3 , CH 2 Br, CHBrCl, CF. 2 CI, C 2 Cl 5 , C 2 F 5 , CHF 2 , CF 2 -CHF 2 , CH 2 CH 2 CI, CH 2 CH 2 Br, C 3 F 7 , C 4 F 9 .
  • Cycloalkyl stands for cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, where the rings can be mono- to doubly methyl-substituted, e.g. 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 1-methylcyclopentyl, 1-methylcyclohexyl.
  • Optionally substituted aryl represents, for example, phenyl, C 1 -C 4 -alkyl-, phenyl, 2-, 3-, 4-tolyl, halophenyl, 4-bromophenyl, 4- chlorophenyl, 4- fluorophenyl, Nitrophenyl, 2-nitrophenyl, 4-nitrophenyl, 1- and 2-naphthyl.
  • Optionally substituted phenoxy, phenylthio, benzyloxy or benzylthio means that the aromatic ring is unsubstituted or mono- to tri-halogenated, such as 2-CI, 2-F, 3-CI, 4-CI, 4-Br, 2,3- Cl 2 , 2,4-Cl 2 , 2,5-Cl 2 , 2,6-Cl 2 , 3,5-C1 2 , 2,4,6-Cl 3 , 3,4,5-Cl 3 or a up to two substituents such as nitro or methyl, 2-NO 2 , 4-NO 2 , 2-CHa, 4-CHa, 2,6- (CHa) 2 , 3,5- (CH 3 ) 2 .
  • cations are, for example, suitable for the salts: Na + , Li + , K + , Mg 2+ , Fe 3+ , NH 4 + , mono- or polyalkylated, hydroxyalkylated and / or arylated ammonium cations, such as diisopropylammonium, tetramethylammonium, tetrabutylammonium, Trimethylbenzylammonium, N, N-dimethylanilinium, trimethyl- (2-hydroxyethyl) ammonium, where the alkyl has 1 to 4 carbon atoms and the aryl radical is a phenyl radical or a benzyl radical.
  • m means 1 to 4, ie 1, 2, 3 or 4.
  • Organic or inorganic compounds such as alkali and alkaline earth metal hydroxides (LiOH, NaOH, KOH, Ca (OH) 2 ), oxides (Na 2 0 Li 2 0, CaO, MgO) can be used as bases or acid-binding agents, hydrides (LiH, NaH, KH, CaH 2 ), amides (LiNH 2 , NaNH 2 , KNH 2 ), carbonates (Li 2 CO 3 , Na 2 CO 3 , CaCO 3 ), bicarbonates (NaHCO 3 ), alkyls (butylLi, CH 3 Li, CH 3 MgCl), -C i -C 5 alcoholates (NaOCH 3 , NaOC 2 H 5 , KOC 2 H 5 , KO-tert-butyl, Mg (OCH 3 ) 2 ), Amines, especially tertiary amines (e.g.
  • trimethylamine triethylamine, diisopropylethylamine, N-methylpiperidine
  • pyridine substituted pyridines (collidine, lutidines, 4-dimethylaminopyridine), bicyclic amines.
  • the reactions can be carried out in the presence of inert solvents or diluents.
  • aliphatic and aromatic hydrocarbons such as toluene, xylenes, cyclohexane, petroleum ether are suitable; halogenated hydrocarbons such as chlorobenzene, methylene chloride, chloroform; Ethers and ethereal compounds such as dialkyl ether (diethyl ether, diisopropyl ether, tert-butyl methyl ether, etc.), anisole, dioxane, tetrahydrofuran; Nitriles such as acetonitrile, propionitrile, N, N-dialkylated amides such as dimethylformamide; Dimethyl sulfoxide; Ketones such as acetone, diethyl ketone, tert-butyl methyl ketone, methyl ethyl ketone, alcohols such as methanol, ethanol, n- and iso-propanol, butanols, especially tert-butanol and mixture
  • the reaction temperature can be changed within wide limits. Depending on the nature of the substituents X, R ', R 2 , R 3 , R 5 , R 6 , R 7 and their number m one works advantageously at temperatures between -20 ° C and 200 C or at the boiling point of the solvent or solvent mixture .
  • Inert gases such as helium, argon, preferably nitrogen, are suitable as the protective gas.
  • the starting compounds are known or can be easily prepared by known methods.
  • the halogen aromatics used or phenols which can easily be converted into them) and anilines are known.
  • the compounds of formula I, according to claim 1 with the proviso that R 4 is different from hydrogen, are prepared, for example, by a 3-anilino-benzisothiazole of formula I, in which R 4 is hydrogen and X, m, R ', R 2 , R 3 , R 5 , R 6 ' R 7 have the meaning given in claim 1, with an acylating or sulfonating agent of the formula IV, in which R 4 has the meaning given in claim 1, except hydrogen and L represents a nucleophilically displaceable leaving group, in bulk or in the presence of a solvent or diluent and, if appropriate, in the presence of an organic or inorganic base at temperatures between -20 ° C and 150 C implemented.
  • Suitable nucleophilically displaceable groups are preferably halogen atoms such as F, Cl, Br, J, sulfonates (methanesulfonate, benzenesulfonate and others), alcoholates (ethylate, benzylate and others) and carboxylates (acetate and others).
  • reaction temperatures are i. a. between -20 ° C and 150 ° C or at the boiling point of the solvent or solvent mixture.
  • One or more inert solvents or diluents may be present in the reaction.
  • aliphatic and aromatic hydrocarbons such as toluene, xylenes, cyclohexane, petroleum ether are suitable; halogenated hydrocarbons such as chlorobenzene, methylene chloride, ethylene chloride, chloroform, tetrachlorethylene; Ethers and ethereal compounds such as dialkyl ether (diethyl ether, diisopropyl ether, tert-butyl methyl ether, etc.) anisole, dioxane, tetrahydrofuran; Nitriles such as acetonitrile, propionitrile; N, N-dialkylated amides such as dimethylformamide; Dimethyl sulfoxide; Ketones such as acetone, diethyl ketone, methyl ethyl ketone, tert-butyl methyl ketone and mixtures of such solvent
  • the new compounds are distinguished by excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes and Basidiomycetes. Some of them are systemically effective and can be used as foliar and soil fungicides.
  • the fungicidal compounds are particularly interesting for combating a large number of fungi on various crop plants or their seeds, in particular wheat, rye, barley, oats, rice, corn, lawn, cotton, soybeans, coffee, sugar cane, fruit and ornamental plants in horticulture and viticulture as well as vegetables - such as cucumbers, beans and pumpkin plants -.
  • the compounds are applied by spraying or dusting the plants with the active compounds or by treating the seeds of the plants with the active compounds. It is used before or after the plants or seeds are infected by the fungi.
  • the fungi or the materials to be protected against fungal attack are treated with a fungicidally effective amount of the active ingredient.
  • the new substances can be converted into the usual formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application forms depend entirely on the purposes; in any case, they should ensure a fine and uniform distribution of the active substance.
  • the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if appropriate using emulsifiers and dispersants, where, if water is used as the diluent, other organic solvents can also be used as auxiliary solvents.
  • solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g.
  • chlorobenzenes paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) ) and water;
  • Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates);
  • Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ether, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
  • the application rates are between 0.02 and 3 kg of active ingredient or more per hectare.
  • the new compounds can also be used in material protection (wood protection), e.g. against Paecilomyces variotii.
  • material protection wood protection
  • amounts of active ingredient of 0.001 to 50 g, preferably 0.01 to 10 g, per kg of seed are generally required.
  • agents or the ready-to-use preparations produced therefrom such as solutions, emulsions, suspensions, powders, dusts, pastes or granules, are used in a known manner, for example by spraying, atomizing, dusting, scattering, pickling or pouring.
  • the agents according to the invention can also be present together with other active ingredients, such as e.g. Herbicides, insecticides, growth regulators and fungicides, or also mixed with fertilizers and applied. When mixed with fungicides, the fungicidal spectrum of activity is enlarged in many cases.
  • active ingredients such as e.g. Herbicides, insecticides, growth regulators and fungicides, or also mixed with fertilizers and applied.
  • Pepper seedlings of the "Neusiedler Ideal Elite" variety after 4-5 leaves had developed well, were sprayed to runoff point with aqueous suspensions which contained 80% active ingredient and 20% emulsifier in the dry matter. After the spray coating had dried on, the plants were sprayed with a conidia suspension of the botrytis cinerea fungus and placed at 22-24 ° C. in a chamber with high atmospheric humidity. After 5 days the disease had developed so strongly on the untreated control plants that the leaf necrosis formed covered the majority of the leaves. The infestation of the leaves was checked.
  • Leaves of pot vines of the "Müller Thurgau” variety were sprayed with an aqueous spray mixture which contained 80% active ingredient and 20% emulsifier in the dry matter.
  • the plants were placed in the greenhouse for 8 days after the spray coating had dried on. Only then were the leaves inoculated with a zoospore suspension of Plasmopara viticola (vine peronospora).
  • the vines were then placed for 48 hours in a steam-saturated chamber at 24 C and then for 5 days in a greenhouse with temperatures between 20 and 30 C. After this time, the plants were again placed in the moist chamber for 16 hours in order to accelerate the sporangium carrier outbreak. Then the extent of the fungal outbreak on the undersides of the leaves was assessed.
  • Leaves of potted plants of the "large meat tomato” variety were sprayed with an aqueous spray liquor which contained 80% active ingredient and 20% emulsifier in the dry matter. After 24 hours, the leaves were infected with a zoospore suspension of the Phytophthora infestans fungus. The plants were then placed in a steam-saturated chamber at temperatures between 16 and 18 ° C. After 6 days the disease had developed so strongly on the untreated but infected control plants that the fungicidal activity of the substances could be assessed.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
EP90112326A 1989-07-05 1990-06-28 3-Anilino-benzisothiazoles et fongicides les contenant Expired - Lifetime EP0406700B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT90112326T ATE104288T1 (de) 1989-07-05 1990-06-28 3-anilino-benzisothiazole und diese enthaltende fungizide.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3922088 1989-07-05
DE3922088A DE3922088A1 (de) 1989-07-05 1989-07-05 3-anilino-benzisothiazole und diese enthaltende fungizide

Publications (2)

Publication Number Publication Date
EP0406700A1 true EP0406700A1 (fr) 1991-01-09
EP0406700B1 EP0406700B1 (fr) 1994-04-13

Family

ID=6384349

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90112326A Expired - Lifetime EP0406700B1 (fr) 1989-07-05 1990-06-28 3-Anilino-benzisothiazoles et fongicides les contenant

Country Status (7)

Country Link
EP (1) EP0406700B1 (fr)
JP (1) JPH03128304A (fr)
AT (1) ATE104288T1 (fr)
CA (1) CA2020416A1 (fr)
DE (2) DE3922088A1 (fr)
DK (1) DK0406700T3 (fr)
ES (1) ES2063204T3 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0478974A1 (fr) * 1990-09-20 1992-04-08 BASF Aktiengesellschaft N-Hétéroaryl-2-nitroanilines
WO1993019054A1 (fr) * 1992-03-26 1993-09-30 Dowelanco Nitro-anilines n-heterocycliques utilisees comme fongicides
WO2006108224A1 (fr) * 2005-04-11 2006-10-19 Murdoch University Composés antiparasitaires
CN111093375A (zh) * 2017-07-03 2020-05-01 拜耳作物科学股份公司 新的基于异噻唑并结构的双环、其制备方法及其用作除草剂和/或植物生长调节剂的用途

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0710215A2 (pt) * 2006-03-31 2011-08-02 Basf Se compostos, composição, métodos para combater ou contolar pragas de animais, para proteger plantas em crescimento contra ataque ou infestação por pragas de animais, e para proteger sementes contra insetos do solo e as raìzes e os galhos das mudas contra insetos do solo e das folhas, e, semente

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0133418A2 (fr) * 1983-08-09 1985-02-20 Ciba-Geigy Ag L'utilisation de 3-acylamino-benzisothiazoles dans la lutte contre les organismes nuisibles
DE3343091A1 (de) * 1983-11-29 1985-06-05 Bayer Ag, 5090 Leverkusen Verwendung von 3-amino-1,2-benzisothiazolen als mikrobizide zum schutz technischer materialien
DE3544436A1 (de) * 1984-12-18 1986-06-19 Ciba-Geigy Ag, Basel Neue dioxide

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3614595A1 (de) * 1986-04-30 1987-11-05 Hoechst Ag Benzoxazolyl- und benthiazolylaniline, verfahren zu ihrer herstellung und ihre verwendung als fungizide mittel

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0133418A2 (fr) * 1983-08-09 1985-02-20 Ciba-Geigy Ag L'utilisation de 3-acylamino-benzisothiazoles dans la lutte contre les organismes nuisibles
DE3343091A1 (de) * 1983-11-29 1985-06-05 Bayer Ag, 5090 Leverkusen Verwendung von 3-amino-1,2-benzisothiazolen als mikrobizide zum schutz technischer materialien
DE3544436A1 (de) * 1984-12-18 1986-06-19 Ciba-Geigy Ag, Basel Neue dioxide

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0478974A1 (fr) * 1990-09-20 1992-04-08 BASF Aktiengesellschaft N-Hétéroaryl-2-nitroanilines
WO1993019054A1 (fr) * 1992-03-26 1993-09-30 Dowelanco Nitro-anilines n-heterocycliques utilisees comme fongicides
WO2006108224A1 (fr) * 2005-04-11 2006-10-19 Murdoch University Composés antiparasitaires
CN111093375A (zh) * 2017-07-03 2020-05-01 拜耳作物科学股份公司 新的基于异噻唑并结构的双环、其制备方法及其用作除草剂和/或植物生长调节剂的用途

Also Published As

Publication number Publication date
CA2020416A1 (fr) 1991-01-06
DK0406700T3 (da) 1994-05-16
EP0406700B1 (fr) 1994-04-13
DE3922088A1 (de) 1991-01-17
ES2063204T3 (es) 1995-01-01
DE59005325D1 (de) 1994-05-19
ATE104288T1 (de) 1994-04-15
JPH03128304A (ja) 1991-05-31

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